Reaction #2553

Reaction equation

4-(4-fluorobenzoyl)piperidine

2-bromoethanol

→

title compound

Yield 78.0%

4-(4-Fluorobenzoyl)-1-(2-hydroxyethyl)piperidine

Yield 78.0%

Solvents

triethylamine

Conditions

Workup

1. 1
   TemperatureAfter 1 hour of heating
2. 2
   Temperatureunder reflux
3. 3
   Othertriethylamine was removed by evaporation
4. 4
   workup.ADDITIONthe resulting residue was mixed with saturated sodium carbonate aqueous solution (40 ml)
5. 5
   Extractionextracted with ethyl acetate
6. 6
   DryingThe resulting organic layer was dried on anhydrous sodium carbonate
7. 7
   Otherthe solvent was removed by evaporation
8. 8
   Otherthe resulting residue was purified

Procedure

In an atmosphere of argon, 4-(4-fluorobenzoyl)piperidine (2.07 g, 10 mmol) was dissolved in triethylamine (30 ml) to which was subsequently added dropwise 2-bromoethanol (1.1 ml, 14.7 mmol) at room temperature. After 1 hour of heating under reflux, triethylamine was removed by evaporation, and the resulting residue was mixed with saturated sodium carbonate aqueous solution (40 ml) and extracted with ethyl acetate. The resulting organic layer was dried on anhydrous sodium carbonate, the solvent was removed by evaporation and then the resulting residue was purified by subjecting it to a silica gel column chromatography (ethyl acetate-methylene chloride:methanol=10:1) to obtain 1.96 g (78.0%) of the title compound in the form of light yellow solid.

Source